Hydrazine hydrate (1:1) → 2-(2-Amino-5-fluorophenyl)acetohydrazide

HRID 50000

反応式

HRID 50000 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.O.[NH2:14][NH2:15]>>[NH2:7][C:8]1[CH:9]=[CH:10][C:2]([F:1])=[CH:3][C:4]=1[CH2:5][C:6]([NH:14][NH2:15])=[O:11]

参加物

3

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 2365665-Fluoroisatin2 回

生成物 1

HCID 690577422-(2-Amino-5-fluorophenyl)acetohydrazide

反応条件

温度
110 °C

実験手順

Hydrazine hydrate (55%, 3000 mL) and 5-fluoroisatin (300 g) were heated to 100° C. An additional 5-fluoro-isatin (500 g) was added in portions (100 g) over 120 minutes with stirring. The mixture was heated to 110° C. and stirred for 4 hours. The mixture was cooled to room temperature and the solids collected by vacuum filtration to give crude (2-amino-5-fluoro-phenyl)-acetic acid hydrazide (748 g). The hydrazide was suspended in water (700 mL) and the pH of the mixture adjusted to <pH 3 with 12 N hydrochloric acid. The mixture was stirred for 12 hours at room temperature. The solids were collected by vacuum filtration and washed twice with water. The product was dried under vacuum to give 5-fluoro-1,3-dihydro-indol-2-one (600 g, 73% yield) as a brown powder. 1H-NMR (dimethylsulfoxide-d6) δ3.46 (s, 2H, CH2), 6.75, 6.95, 7.05 (3×m, 3H, aromatic), 10.35 (s, 1H, NH). MS m/z 152 [M+1].

後処理

  1. stirringstirred for 4 hours
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationthe solids collected by vacuum filtration

出典と根拠

ORDレコード
ord-b0ffcea2be874f39976f0c9c68ec97ac
出典データセット
uspto-grants-2004_03
特許番号
US06710067B2

関連ノート

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